


Never Have I Ever

by Lilith_Lucius



Category: Descendants (Disney Movies)
Genre: Anal Sex, Fluff, Friends With Benefits, Multi, Pansexual Harry Hook, Pansexual disaster, Sex, Slight bit of bondage, Smut, Swearing, Teasing, Vaginal Sex, orgy?, virgin
Language: English
Status: Completed
Published: 2019-08-13
Updated: 2019-08-13
Packaged: 2020-08-29 19:49:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,594
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20231932
Author URL: https://archiveofourown.org/users/Lilith_Lucius/pseuds/Lilith_Lucius
Summary: Mal, Ben, Evie, Doug, Uma, Gil, Jane, Carlos, Jay and Lonnie all find out that Harry is still a virgin and decide to do something about it, at first it was harder than they all thought but something changed and Harry was quite willing to accommodate everyones desires.And possibly make everyone think they slept with him first.





	Never Have I Ever

**Author's Note:**

> This is one of my many fanfiction from my Tumblr 'HarryandhisHook'
> 
> I decided to move all of them over to here after a lot of thinking, since the whole flagging NSFW stuff happened, I know it was a while ago but I've finally got around to doing it and I'd rather not be flagged for simple fanfics.
> 
> I will still be posting all my stuff on Tumblr ... when I make more stuff but a lot of it will be on here from now on, I'll be finding other websites to post some other stuff too but most of it will be mainly here.
> 
> Thank :D
> 
> This was requested by a user on Tumblr - @microscopesandscrewdrivers - Can I have a funny little fic where Harry is the last of his friends to lose his virginity and tries everything until all hits friends make it a competition to sleep with him first and he gets laid like 10 times that day? Odd and specific but I just need it for reasons.

Never have I ever wasn’t complete without alcohol and since, one, they were under age and two, Fairy God Mother had banned anything they couldn’t legally have, that didn’t stop any of them. Evie, being the clever girl she is, had managed to make everyone homemade alcoholic apple cider, promising everyone it would not be poisoned and Jay, being the sneaky thief he is, had manged to steal an entire crate of beers and even some good old spirits for them to down.

So now, Mal, Evie, Carlos, Jay, Harry, Uma, Gil, Lonnie, Doug, Ben and even Jane were sat in Harry and Gils room, drinking themselves stupid, laughing, flirting and basically just being teenagers but it wasn’t until Uma and Mal made a very shocking confession that everyone decided that maybe playing never have I ever wouldn’t be too bad of an idea. And now, with full glasses and everyone sat in a sort of circle, Harry refused to sit on the floor and stayed on the bed as everyone tried to get everyone else out with the chance to get some juicy gossip from each other.

“Okay okay, so now we know that Jay used to have dirty dreams about Carlos, we just need to see how long it’ll take them to bang” Uma chuckled as she took a little sip of her drink, watching as Jays eyes widened, stuttering out protests and Carlos blushed hard, hiding his face in the crook of Janes neck as the innocent girl laughed hysterically, “Since we’ve found out dirty little secrets about everyone except Harry, we’re gonna have to delve deeper, since it’s Janes turn, you can try and get Harry to reveal his deepest darkest secret” the teal haired girl said, watching the young fairy bite her lip, it was no secret that Jane was quite innocent when it came to sexual encounters but as they had just learnt today, she’s not as innocent minded as they had originally thought her to be,

“Erm … well, you guys know I’m not that good at this game, my last one was about disobeying teachers, I doubt I’m going to get much out of him, Uma” Jane quietly said, looking down at her lap as Carlos pulled back from hiding his face in her neck to look at her,

“You’re not that bad at thinking them up, I mean, you did find out that I have never disobeyed a teacher, even on the isle” he smiled and took her hand in his, “Look, even the innocent ones are fun because it shows everyone just how much of a goody two shoes everyone is” he chuckled and shuffled closer, wrapping his arm around her waist, pressing his fingers softly into her side, gaining a little squeak from her, “So, just say the first one that pops into your head, I bet it won’t be that bad and if it is a soft one, then whoever is the goody two shoes and have done it, once they drink then they’ll just have to deal with the fact that you outed them” Carlos smiled and kissed her cheek softly, making Jane chuckle and smile happily,

“Okay, fine, just let me think for a minute” Jane sat there, biting her lip as she looked around everyone, trying to think of anything, looking at Harry didn’t give her anything, neither did looking at anyone in the room, it wasn’t until she spotted Ben kissing Mal’s neck playfully that she finally thought of one, even if it wasn’t a massive one, it was something, “Fine then, never have I ever had sex, drink up if you have” she giggled, waiting a moment as she looked at everyone, Mal’s eyes drifted to look at Ben, biting her lip before they both lifted the glasses to their lips, taking a sip and giggling as they did. Her gaze then moved to Evie and Doug, sitting hand in hand, trying to be discreet about taking their sips. She eventually passed her eyes over Uma as she took quite a large swig of hers confidently but it surprised her when she looked at Gil whose cup was pressed against his lips, even Jane didn’t see Gil ever having sex, he was too adorable. Finally, without any hesitation, she watched as Jay and Lonnie chugged the remainder of their drinks, winking at each other which definitely did not surprise her. She was finally pulled back into the game when Carlos nudged her arm, she blushed hard, looking up into his eyes before nodding, both lifting their drinks and taking small sips, causing everyone in the room to cheer and comment on it,

“Finally!”

“When did this happen?!”

“DETAILS!”

All the shouts made the two blush even more, turning to look anywhere except at each other, it finally settled down when Lonnie pipped up, “Erm guys”, the sudden voice made everyone look to her pointed finger, leading their gazes to Harry, it would have confused everyone if they hadn’t noticed that his cup was sat on the bedside table in the exact same position it had been previously, not touched, the small detail caused everyone’s brain to flash some sort of alarm that there was something not quite right. For a moment, no one spoke up until the soft melodic voice of Evie finally broke the silence,

“Harry … did you drink?” she questioned, it was obvious that Harry had drifted into a world of his own when his head suddenly turned to look at Evie,

“Huh, oh … erm … no …” his gaze drifted down to his lap causing everyone to notice how he was fiddling with the hem of his shirt, it didn’t take long for everyone to simultaneously shout,

“YOU’VE NEVER HAD SEX?!” the sudden exclaim made Harry look up, his expression held a mix of anger and slight embarrassment, he knew he had been caught but he was going to try not to make it into anything weird or at least anything to discuss,

“It’s not like it’s a big deal, I mean we are all still teenagers so there’s no rush or anything…” Harry finally said after a moment of silent stares from everyone, Uma nodded in agreement,

“Well, he does have a point, we are teenagers but still, I think everyone’s just shocked at the fact that, you, Harry fucking Hook, the most flirtatious pirate everyone has met, the guy who constantly tells every girl he meets how he could rock their world in one night, has never actually rocked anyone’s world in one night” she commented, she knew he was right but even she had to admit how strange that was, “Now I feel like we need to take your V card” she chuckled, causing everyone to giggle only making Harry blush hard,

“I mean, it’s not like I haven’t tried, I just … I kinda always liked the whole thing of true love, I don’t really want to just give it to some random girl or guy, I kinda wanna give it to someone special” he admitted causing all the girls to fangirl, even Lonnie, the most tom boyish one of them all,

“Alright, let’s continue with the game so we don’t embarrass poor Harry further” Mal chuckled as sat back, snuggling up to Ben and starting up the game once more.

~~~

It didn’t take too long before everyone from the group were trying to get an oblivious Harry into bed, Mal and Ben tried to subtly suggest he join the both of them in bed but Harry thought they were joking and brushed it off, after that, everyone decided to change strategies, nothing worked, even when Jay flat out asked Harry if he wanted to fuck, which obviously didn’t work, it also made Harry realize what they were doing, he would have been angry at them but something about the situation made him feel quite proud of himself.

It was later that night, everyone was in their rooms except for a young pirate captain who was sat on the edge of the bed of her first mate who was laid spread out across the blankets, listening to his complaints of the day, he had told her about feeling a little proud but he also told her about how he felt like everyone would probably just use him, feeling like once they took his virginity, they wouldn’t care about him anymore, he felt lost and only Uma could help him,

“Harry, you know that wouldn’t happen, listen, everyone just wants to help, we understand what you mean about the fact we’re still young but you have your whole life ahead of you, you can’t wait forever for your true love, they may come tomorrow or next year” she smirked and nudged him with her elbow, “Anyway, you might as well get some practice in and make your true love worship your amazing skills” Harry chuckled and sat up fully against the headboard,

“I guess ye’re right but like I said, I just don’t want to give it to anyone, I want to give it to someone I trust, someone I love” he sighed and laid his head back against the wall, “I mean, I’m not going to lie but for a while, I have been starting to get quite … frustrated” he admitted, looking towards the window, watching as the sun started to set. Uma sighed and shuffled closer, taking his hand in hers,

“Harry, you know we all love you, we wouldn’t force you to do anything but Harry, we are all offering you a way to relieve yourself” she bit her lip and looked down at Harry’s chest, looking over his muscles, she had no idea why he had taken off his shirt literally minutes after she had arrived there but she wasn’t complaining, she took a deep breath and leaned forward, running her hand over his muscles, “all of us want to help you but only if you want it” Harry looked down at the hand touching him, his breath hitched as Uma slowly climbed fully on the bed, inching closer to him, his gaze jumped up to Uma who was now watching his expression, his heart pounding as their faces were soon only inches apart and Uma’s voice became nothing but a whisper, “Let me help you, Harry” they stared into each other’s eyes for a few moments before Harrys eyes flicked down to her lips as he leaned their foreheads together.

The room was silent, nothing was said as they just leaned against each other, Uma was slowly coming to the decision that this was probably a bad idea, if Harry wanted this, he would have said, he would have tried to. She closed her eyes and started pulling away but was taken by surprise when a large hand tangled through her hair, pulling her back forward, but it wasn’t their foreheads that connecting, something soft pressed against her lips, when her eyes opened, she could see that Harrys were closed and his lips were softly pressed against hers. Soon, her eyes were closed again and without breaking the kiss, her leg moved over Harrys to straddle him, closing the distance of their bodies and causing their kiss to deepen. Their tongues danced in each other’s mouths, their moans filled the silent room as they indulged in the feeling of each, savouring the taste.

Harry’s hands slowly moved from Uma’s hair, his fingers gently running down her clothed back, a little moan escaping her mouth as his hand wrapped around her ass, giving a soft squeeze. Uma’s hand suddenly gripped the strands of the red pirates’ hair, pulling softly, causing his head to fall back and a gasp to slip past his lips. Their lips parted as hers moved to his neck, her lips grazing the skin around his jaw and Adam’s apple, making the pirate in front of her a moaning mess. The moans soon grew louder when Uma’s teeth nipped at the different parts of his neck, his hands becoming a little more desperate as they gripped her ass harder.

Uma realized just how turned on and desperate Harry was getting when the moment she moved her hips, the feeling of something hard, pressed against her and a soft moan ripped through her throat causing Harrys little friend to twitch, needing attention.

In a moment, it was like all the confidence in the world hit Harry as his hands grabbed the bottom of her shirt, almost ripping it off as he pulled it over her head and throwing it to the side. The sudden change in Harry made Uma stare at him in amazement but it didn’t last long as a gasp left her lips and her bra was ripped from her breast as a pair of soft lips attacked them quite roughly,

“H-Harry” her body tingled as his teeth brushed over her nipples, causing her to arch her back into him, her nails gripping tightly onto his shoulders, only making Harry grow bolder. With barely any strength, he flipped them both over, pinning her to the bed and leaving as many bruises as possible to her breasts, his hips rolling hard against her, causing the both of them to let out a few moans.

It didn’t take too long after that for Harry’s hands to pull at Uma’s trousers, easily taking them from her body, leaving her in nothing but her panties underneath him. The pirate sat back and stared at her body, taking in every inch of her, his eyes appreciating every little tiny piece of her body which made Uma blush and look away, trying to press her legs together and cover her chest but obviously, the other wasn’t about to let that happen as he grabbed her arms and pinned them next to her head, pressing his body back between her legs,

“Uma, ye’ are absolutely the most beautiful creature I have ever laid me eyes on … and I want ye’ to have me virginity, I want to give it to ye’” he moved his head, nuzzling her neck softly, “I trust ye’ Uma, I love ye’” he whispers as he slowly undoes his trousers, kissing her neck gently. Uma blushed, running her hands over his back and through his hair, letting out a few breathy moans before speaking,

“God, Harry, I-I love you too, I’ve always loved you” throughout the night, the only noises in the room were the screams of pure ecstasy from both Uma, the one screaming out for more and Harry, the one with the energy to go for the rest of the night.

~~~

It was definitely noticeable that Harry had a spring in his step now, whether it was obvious or not, it made anyone around him have a smile on their face. His classmates had also started noticing that Harry was with Uma a lot more than usual, officially, they weren’t a couple, they hadn’t even talked about it but both of them knew they had taken a new a large step in the relationship, however, they hadn’t told any of their little group about their encounter and since that day, everyone had been making plans on who can get Harry into bed first and well … all of them now think each of them have.

First, it was Evie, since Evie was the daughter of the ‘fairest queen’, she decided to take the seduction route, she had planned an entire day of seducing him but the moment she started touching him, Harry had dragged her to his room, pinning her against the wall and ravishing her body, somehow having the energy of a god. All night, Harry was in control, his voice controlling her, his hands pinning her and his tongue making her say things no one would have ever expected her to dare think.

Second, it was Mal and Ben, they decided to try the approach of asking and to their amazement, Harry instantly agreed. When they got to the bedroom, Harry was completely the centre of attention but as the couple soon found out, he was in control. For Harry, Mal was easy to make scream, all she needed was a scarf wrapped around her wrists and a pair of rough hands but Ben, he was quite a lot harder since Harry had never been with a guy before, luckily, Mal was there to help them both out … she may have fucked Ben a few times … it took them both a few moments to get used to it but it didn’t take long before Ben was screaming for more.

The next pair took Harry by surprise more than any of the other, Lonnie and Jane gave him the proposition to sleep with them both at the same time, it took a while to agree once they had said their boyfriends were fine with it and once they had arrived at the room, it was amazing how they didn’t have a noise complaint, Harry was honestly amazed they could walk in the morning since they were left shaking and panting by the end of the night.

Next, Carlos and Gil, it was more of an accident that they both slept with Harry at the same time, the only reason they did was because Gil walked in the room while Harry had Carlos pinned underneath him, pressing his lips on any sensitive part of his naked body. By the end of the night, Harry had managed to make them both pass out from exhaustion … also making him take Gils bed since there was no space on his.

And lastly, Jay, Harry laughed at the fact that Jay was last but when Jay had forcefully pushed Harry into the bedroom, he knew it was going to be a massive change, this time, Jay was in control, Harry couldn’t do anything but then again, he wasn’t complaining too much. It wasn’t until Jay had stripped Harry and flipped him onto his stomach that the pirate knew he was going to be feeling new things, things unlike anything he had ever felt before and as soon as he felt Jay inside him, he screamed, not a bad scream but one that was definitely pure pleasure, anyone living in the rooms next door could definitely tell that this time, Harry was the one that was being put through the pleasures of sex and clearly, he was enjoying it.

Now, they were all back in Harry and Gils room, the smell of sex still lingering, a few drinks in hand and a lot of jokes, it wasn’t until Harry smirked and looked to Uma who winked back at him, that he decided to mess with everyone,

“I’ve never been so happy in me life, I’m so glad ye’ took me virginity” he spoke out loud, letting everyone think he was talking to them, as he stared down at his drink, pretending to be all shy and happy, it wasn’t until he heard a collective ‘you’re welcome’ that he finally looked up with a biggest smirk on his face, obviously causing everyone to start having a massive debate on who took his virginity, everyone except Doug who was sat there laughing, Harry rolled his eyes and moved over to Doug, sitting next to him,

“So, I have to ask, everyone tried to take me virginity, except ye’, why?” Harry asked, looking to the boy next to him who was calming down from laughing so hard. It took him a moment before he finally spoke up,

“Well, I knew that everyone was doing this, trying to bed you first, I won’t deny, I did try but when you denied me, I decided to just let you be … and also the fact, I didn’t want to sleep with someone I’ve only just became friends with, I felt like it could have ruined something and I really consider you a close friend” he smiled and looked at the pirate, leaning back on his arm, Harry smiled and leaned over, kissing his cheek softly,

“Thank ye’, ye’re the first person who’s ever been so honest with me, I appreciate it man” he leaned back on his arms as well, watching as everyone argued, except Uma, who was currently on the floor dying of a laughing fit,

“So, if you don’t mind me asking, who actually did take your virginity?” he asked, looking around the room at everyone who was still convinced each of them had. Harry chuckled and took a sip of his drink,

“Well, technically, Jay did take one of me virginities since he topped but the real person who took me virginity was Uma, I mean, look at her laughing, she knows since I physically told her she was taking it” he smiled and laid back on the floor, chuckling to himself,

“You going to tell everyone?” Doug asked, watching the pirate as he laid on the ground, way too smug,

“Nah, let them argue, it’s more fun that way” he smirked and closed his eyes, it wasn’t until he felt his legs being grabbed and the sensation of being dragged into the middle of the circle that he opened them again, hearing just one statement before everything became crazy,

“Well, how about we just torture Harry into telling us, I mean, there is only so much teasing he’ll be able to take before giving in to us” they smirked as they watched Harry try to scramble away and that night was also the first and maybe not last time they had a bit of an orgy.


End file.
